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[1]旷歧轩 谭璐 罗禹 冯丹 周煜 郭大乐 任波** 邓赟**.川芎内生真菌Fusarium proliferatum的化学成分[J].应用与环境生物学报,2021,27(03):1-12.[doi:10.19675/j.cnki.1006-687x.2020.06069]
 KUANG Qi-xuan,TAN Lu,LUO Yu,et al.Chemical constituents of the endophytic fungus Fusarium proliferatum from Ligusticum chuanxiong Hort.[J].Chinese Journal of Applied & Environmental Biology,2021,27(03):1-12.[doi:10.19675/j.cnki.1006-687x.2020.06069]
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川芎内生真菌Fusarium proliferatum的化学成分()
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《应用与环境生物学报》[ISSN:1006-687X/CN:51-1482/Q]

卷:
27卷
期数:
2021年03期
页码:
1-12
栏目:
研究论文
出版日期:
2021-06-25

文章信息/Info

Title:
Chemical constituents of the endophytic fungus Fusarium proliferatum from Ligusticum chuanxiong Hort.
作者:
旷歧轩1 谭璐1 罗禹2 冯丹1 周煜1 郭大乐1 任波1** 邓赟1**
1成都中医药大学药学院 中药材标准化教育部重点实验室,四川省中药资源系统研究与开发利用重点实验室-省部共建国家重点实验室培育基地 成都 611137
2西南医科大学药学院 泸州 646000
Author(s):
KUANG Qi-xuan1 TAN Lu1 LUO Yu2 FENG Dan1 ZHOU Yu1 GUO Da-le1 REN Bo1** DENG Yun1**
1 Key Laboratory of Standardization of Chinese Herbal Medicine, Ministry of Education, State Key Laboratory Breeding of Systematic Research Development and Utilization of Chinese Medical Resources, Co-founded by Sichuan Province and MOST, Pharmacy Department, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China
2 School of Pharmacy, Southwest Medical University, Luzhou 646000, China
关键词:
川芎内生菌Fusarium proliferatum化学成分细胞毒活性
Keywords:
Ligusticum chuanxiong hort. endophytic fungus Fusarium proliferatum chemical constituents cytotoxicity
DOI:
10.19675/j.cnki.1006-687x.2020.06069
摘要:
研究川芎的内生真菌 Fusarium proliferatum 的次代谢产物及其细胞毒活性。采用硅胶柱层析、中压反相硅胶柱色谱、制备液相色谱等方法从该菌的发酵产物的乙酸乙酯萃取相中分离得到23个化合物。通过波谱技术分析鉴定化合物结构,分别为7-氧代-β-谷甾醇(1),7-氧代-β-豆甾醇(2),过氧化麦角甾醇(3),9,11-脱氢过氧化麦角甾醇(4),5α,6α-环氧-3β-麦角甾-22-烯-7-酮(5),5α,6α - 环氧-3β,8β,14α-羟基-5α-麦角甾-22E-烯-7-酮(6),3β-羟基-(22E,24R)-麦角甾-5,8,22-烯-7-酮(7),(4S,17R)-4-羟基-17-甲基甾醇(8),(3β,5α,6β,22E)-麦角甾-7,22-二烯-3,5,6-三醇(9),白僵菌素(10),对羟基苯甲醛(11),环- (L)-脯氨酸-(L)-甘氨酸(12),环-甘氨酸-(D)-苯丙氨酸(13),环-2-羟基-脯氨酸-甘氨酸(14),环-(L)-苯丙氨酸-丙氨酸(15),9-十八碳烯酸-2’,3’-二羟基丙酯(16),环-4-羟基-(D)-脯氨酸-(L)-苯丙氨酸(17),环-4-羟基-(L)-脯氨酸-(D)-苯丙氨酸(18),环-4-羟基-(L)-脯氨酸-(L)-苯丙氨酸(19),环-(L)-脯氨酸-(L)-亮氨酸(20),环-(D-脯氨酸-D-苯丙氨酸)(21),环-(L-脯氨酸-L-苯丙氨酸)(22),白僵菌酮(23)。采用 MTT 法测试化合物 1 - 7 和化合物 10 的细胞毒活性,结果显示化合物 3 和化合物 5 表现出对MV4-11细胞株的抑制作用,IC50值分别为31.73 ± 2.08和14.81 ± 1.89 μmol/L 。化合物 4 和化合物 10 表现出对 MV4-11,HCT116,HGC-27 细胞株不同程度的抑制活性,化合物 4 对三种细胞株的IC50分别为22.87 ± 2.41、29.58 ± 1.96、48.85 ± 2.05 μmol/L,化合物 10 对三种细胞株的IC50分别为4.94 ± 1.17、3.81 ± 1.62、10.06 ± 1.49 μmol/L。本研究分离得到的单体化合物主要为甾类与环二肽类,其中化合物 1 - 9,13 - 15,17 - 22 从该菌种中首次分离得到,丰富了镰刀属真菌次生代谢产物的化学结构的多样性,可以进一步从生物间化学行为的角度探究川芎与其内生菌的相互作用规律和机制。
Abstract:
This study focused on the secondary metabolites of endophytic fungus F. proliferatum from Ligusticum chuanxiong hort. and their cytotoxicity against three tumor cell lines. 23 compounds were isolated and purified from the ethyl acetate extract of the fermentation broth by column chromatography, medium-pressure reversed-phase silica gel column chromatography, preparative HPLC, and other methods. Their structures were elucidated based on the comprehensive spectroscopic analysis. The compounds were identified as follows: 7-Oxo-β-Sitosterol ( 1), 7-Oxo-β-stigmasterol ( 2), Ergosterol peroxide ( 3), 9,11-Dehydroergosterol peroxide ( 4), 5α,6α-epoxy-3β-hydroxyergosta-22-ene-7-one ( 5), 5α,6α-Epoxy-3β,8β,14α-Trihydroxy-5α-ergost-22E-en-7-one ( 6), 3β-Hydroxy-(22E,24R)-ergosta-5,8,22-trien-7-one ( 7), (4S,17R)-4-Hydroxy-17-methylincisterol ( 8), (3β,5α,6β,22E)-ergosta-7,22-diene-3,5,6-triol ( 9), beauvericin ( 10), 4-hydroxybenzaldehyde ( 11), cyclo-(L-prolyl-L-glycine) (12), cyclo-(Gly-D-Phe) ( 13), cyclo-(2-hydroxy-Pro-Gly) (14), cyclo-(L-Phe-Ala) (15), 9-Octadecenoic acid (Z)-,2’,3’-dihydroxypropyl ester (16), cyclo-(4-hydroxy-D-prolyl-L-phenylalanine) (17), cyclo-(4-hydroxy-L-prolyl-D-phenylalanine) (18), cyclo-(4-hydroxy-L-prolyl-L-phenylalanine) (19), cyclo-(L-Pro-L-Leu) (20), cyclo-(D-Pro-D-Phe) (21), cyclo-(L-Pro-L-Phe) (22) and bassiatin (23). The MTT method was applied to uate the cytotoxicity of compounds 1 - 7 and compound 10 against MV4-11, HCT116 , and HGC-27 cell lines. The result showed that compound 3 and compound 5 exhibited inhibitory activity against MV4-11 cell lines with IC 50 values of 31.73 ± 2.08 and 14.81 ± 1.89 μmol/L, respectively. Compound 4 and compound 10 showed significant inhibitory activity against MV4-11, HCT116 and HGC-27 cell lines . The IC50 of 4 were 22.87 ± 2.41 , 29.58 ± 1.96 and 48.85 ± 2.05 μmol/L, and the IC50 of 10 were 4.94 ± 1.17, 3.81 ± 1.62 and 10.06 ± 1.49 μmol/L, respectively. The compounds isolated are mainly steroids and cyclic dipeptides. Compounds 1 - 9, 13 - 15 and 17 - 22 were isolated from the fermentation of Fusarium proliferatum for the first time. The diversity of the chemical structure of the secondary metabolites of F. proliferatum has been expanded on further research that exploring the interaction mechanism between Ligusticum chuanxiong hort and endophytic fungus from the chemical signal transmission.

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备注/Memo

备注/Memo:

收稿日期 Received: 2020-06-29 接受日期 Accepted: 2020-08-29
国家自然科学基金面上项目(81973460)、四川省科技厅应用基础研究项目(2018JY0186)、四川省教育厅科研项目(18ZA0191)和成都中医药大学杏林学者学科人才科研提升计划(BSH2018008)资助

**通讯作者 Corresponding authors (E-mail: renbo@cdutcm.edu.cn; dengyun@cdutcm.edu.cn)
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更新日期/Last Update: 2020-09-10